Acetone → 2,4-Diiodopyrimidin-5-amine

Participants

Reaction Conditions

Reaction Steps

A 4-necked roundbottom flask was charged with acetone (9.8 L), 2,4-dichloro-5-nitropyrimidine (670 g, 3.45 mol), and sodium iodide dihydrate (1929.6 g, 10.38 mol). Hydrogen iodide (67 ml, 40%) was then added dropwise. The resulting solution was allowed to react, with stirring, for three hours while the temperature was maintained at 20-30° C. Iron (978.6 g, 17.48 mol) was then added followed by the dropwise addition of water (300 ml). The resulting solution was allowed to react, with stirring, for an additional two hours while the temperature was maintained at reflux. The resulting slurry was filtered and the filtrate was concentrated under reduced pressure. The resulting aqueous solution was extracted four times with five liters of ethyl acetate. The combined organic layers were concentrated under reduced pressure. The resulting residue was purified via silica gel chromatography eluting with 1:1 ethyl acetate/petroleum ether to afford the title compound.

Provenance & Evidence